JPH07109250A - Beta-nitrophenylethylamine derivative and antibacterial mildew-profing agent - Google Patents

Abstract

PURPOSE:To provide a novel beta-nitrophenylethylamine derivative having high antimicrobial activity against fungi and bacteria, especially adhesive marine bacteria, exhibiting growth inhibiting activity against fungi and bacteria in vitro and useful as an antibacterial mildew-proofing agent. CONSTITUTION:A beta-nitrophenylethylamine derivative expressed by the formula I (R is alkyl), e.g. ethyl N-(2-(4-nitrophenyl)ethyl]carbamate of the formula II. The compound of the formula I can be produced by reacting beta- nitrophenylethylamine with various acid halides. The antibacterial mildew- proofing agent containing the beta-nitrophenylethylamine derivative of the formula I as an active component is usable for the sterilization and disinfection of skin, hair, clothes, tableware, medical appliance, etc., and useful as a sterilizing and deodorizing agent for industrial production process or livestock barn and a water-treating disinfectant and slime-controlling agent for swimming pool, cooling water, etc.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a novel β-nitrophenylethylamine derivative and an antibacterial and antifungal agent containing the same as an active ingredient.

[0002]

Molds and bacteria cause various diseases, and also cause various pollution in a wide range of industries such as agriculture, forestry and fisheries, industries, and places of daily life, such as trees, fruit trees, vegetables, and grasses caused by plant pathogens. It causes diseases such as slime formation by filamentous fungi and marine bacteria. Various antibacterial agents (for example, polyoxin, blasticidin, griseofulvin) are used for protection, but not only is there always a demand for more effective, safe and easily available materials, but it is also related to resistant species. Therefore, the discovery of new substances is indispensable. In particular, a low molecular weight substance that can be easily synthesized is advantageous in terms of supply and safety to the ecosystem after use. In addition, the need for non-halogen substances that are gentle to the global environment is increasing worldwide.

[0003]

[Problems to be Solved by the Invention] Therefore, in this study, β
-By synthesizing various derivatives of phenylethylamine, it is an object to develop a substance having high antibacterial activity against fungi and bacteria, especially marine adherent bacteria.

[0004]

DISCLOSURE OF THE INVENTION The present inventors have found that the above-mentioned general formula (1) derived from β-nitrophenylethylamine is used.
The present invention was completed by finding that the novel β-nitrophenylethylamine derivative represented by the formula (3) shows in vitro growth inhibitory activity against fungi and bacteria.

That is, the present invention has the general formula

[0006]

[Chemical 3]

The present invention provides a β-nitrophenylethylamine derivative represented by the formula (wherein R represents an alkyl group).

Examples of the alkyl group represented by R in the above general formula (1) include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, a pentyl group and a hexyl group. it can.

The novel β-nitrophenylethylamine derivative represented by the above general formula (1) of the present invention can be obtained by reacting β-nitrophenylethylamine with various acid halides. The raw material β-nitrophenylethylamine is synthesized by a known method (Ehrlich et al., B
er., 1912, 45 , 2428). Alternatively, β-nitrophenylethyl isocyanate or β-nitrophenylethylcarbamoyl chloride (Belg. 611,900, June 2
2, 1962; Swiss Appl., Dec. 23, 1960 and Oct. 20, 1
It is also synthesized by adding various alcohols to 961).

Specific examples of the compound contained in the above general formula (1) in the present invention include methyl N- [2- (2-nitrophenyl) ethyl] carbamate methyl N- [2- (3-nitrophenyl). Ethyl] carbamate methyl N- [2- (4-nitrophenyl) ethyl] carbamate ethyl N- [2- (2-nitrophenyl) ethyl] carbamate ethyl N- [2- (3-nitrophenyl) ethyl] carbamate ethyl N -[2- (4-Nitrophenyl) ethyl] carbamate propyl N- [2- (4-nitrophenyl) ethyl]
Carbamate isopropyl N- [2- (4-nitrophenyl) ethyl] carbamate butyl N- [2- (4-nitrophenyl) ethyl] carbamate and the like can be exemplified.

In the antibacterial and antifungal agent of the present invention, the β-nitrophenylethylamine derivative represented by the general formula (1) of the present invention can be used as it is, but it is usually used in the form of a preparation. . For formulation, conventional diluents, carriers, fillers, additives and the like can be used, and the methods generally used in this field can be applied. It can be used in the form of liquid, emulsifier, solid, powder, wettable powder and the like. The fungicide containing the β-nitrophenylethylamine derivative of the present invention as an active ingredient, in addition to the human body and animals, has a wide range of industries such as agriculture, forestry and fisheries, industry, and diseases caused by plant pathogens such as trees, fruit trees, vegetables, and grasses, It can be used to protect slime formation by filamentous fungi and marine bacteria. Specifically, it can be used for disinfecting and sterilizing skin, hair, clothes, tableware, medical equipment, etc., and also water such as disinfecting deodorants for industrial manufacturing processes or livestock buildings, plant antibacterial agents, pools, cooling water, etc. It is useful as a disinfectant for treatment and a slime control agent.

[0012]

EXAMPLES The present invention will be described in more detail with reference to Examples and Test Examples. However, the present invention is not limited to these.

Example 1: Ethyl N- [2- (4-
Synthesis of [nitrophenyl) ethyl] carbamate

[0014]

[Chemical 4]

Β-p-nitrophenylethylamine hydrochloride (2.0 g, 9.9 mmol), dimethylaminopyridine (0.1
g) and pyridine (4.5 g) were placed in a 100 ml eggplant-shaped flask, the atmosphere was replaced with argon, and 50 ml of dichloromethane was added to make a uniform solution. Ethyl chloroformate under ice cooling (2.6g, 24mmol)
Was slowly added and reacted for 50 minutes, then the reaction solution was concentrated under reduced pressure and partitioned with ethyl acetate and water (100 ml each). The ethyl acetate layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain compound (2) as a yellow solid (2.4 g). mp: 92.5-93.0 ° C (recrystallized from toluene) ¹ H-NMR (CDCl ₃ , ppm): δ1.18 (3H, t, J = 7Hz), 2.90 (2H, t, J =
7Hz), 3.43 (2H, q, J = 7Hz), 4.89 (1H, brs), 7.33 (2H, d, J = 7H
z), 8.11 (2H, d, J = 7Hz). Mass (m / z): 238 (M ⁺ ).

Test Example 1: Antifungal test Black spores of black mold (Aspergillus niger (IFO 4407))
Suspend 1 platinum loop in 1 ml of physiological saline and
It was applied to a potato dextrose agar plate (10% tartaric acid 14 ml / l added) prepared in an 85 mm petri dish. 10 μl of a methanol solution containing the compound (2) at a predetermined concentration was placed on an autoclave-sterilized circular filter paper (diameter 6 mm) and gently placed on the flat plate. After culturing at 25 ° C for 3 days, the diameter of the inhibition circle was measured. The results are shown in Table 1.

[0017]

[Table 1]

Test Example 2: Antibacterial test Liquid medium (peptone 0.5%, yeast extract 0.1%, 1 /
Rhodospirillum cultivated in artificial seawater (2 concentration) for 3 days
Sarekishigensu (Rodospirillum sarexigens SCRC-113
(FERM P-13599)) 100 μl of the culture solution was applied to a marine agar plate prepared in a petri dish having a diameter of 85 mm. 10 μl of a methanol solution containing the compound (2) at a predetermined concentration was placed on an autoclave-sterilized circular filter paper (diameter 6 mm) and gently placed on the flat plate. After culturing at 25 ° C for 3 days, the diameter of the inhibition circle was measured. The results are shown in Table 2.

[0019]

[Table 2]

[0020]

INDUSTRIAL APPLICABILITY The compound of the present invention has a strong growth inhibitory action against mold and bacteria and is expected as an antibacterial and antifungal agent.

Claims (2)

[Claims] 1. A general formula: (In the formula, R represents an alkyl group) A β-nitrophenylethylamine derivative. 2. A general formula: An antibacterial and antifungal agent comprising a β-nitrophenylethylamine derivative represented by the formula (wherein R represents an alkyl group) as an active ingredient.